Prior whiteboard applications have been used via computer systems, enabling displayed content to be drawn upon or otherwise manipulated via input devices such as mice, trackpads, touchscreens, etc. In this way, the whiteboard application can provide the functionality of a physical dry-erase or chalkboard in a computing context. Whiteboard applications are commonly used in collaborative settings such as meetings, brainstorming sessions, classrooms, etc. Therefore, in some instances a plurality of users may manipulate content presented via the whiteboard application in one or more sessions. The data associated with the manipulation of the content may be saved locally by the computing system. However, the computing system using the whiteboard application may be used by a number of users. Therefore, storing the data locally may create security concerns. Furthermore, storing the data locally may increase the amount of storage needed in the computing system. Therefore, offloading the content may be desirable to alleviate the security concerns and decrease local storage needs. However, offloading the content to a portable storage device (e.g., thumbdrive), for example, can be cumbersome and require many awkward steps involving numerous input commands. Consequently, it may be inefficient for one or more users to offload the content quickly during a collaborative session. As a result, users may find interaction with the whiteboard application slow and awkward. Moreover, it may be difficult to upload the offloaded content for use in a subsequent whiteboard session, leading to additional interactive inefficiency.